Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
  • C07D213/643—2-Phenoxypyridines; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
  • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

• the present invention relates to a novel derivative of phenoxypropionic acid ester, a manufacturing process therefor, a selective herbicide containing said chemical compound as the active constituent and a herbicidal process using said herbicide.
• Many derivatives of the phenoxypropionic acid ester have been reported to have herbicidal effect, including, for example, 2-[4-(4-trifluoromethyl- phenoxy)-phenoxy] propionic acid methyl ester, 2-[4-(2,4-dithlorophenoxy)-phenoxy] propionic acid methyl ester, 2-[4-(3,5-dichloro-2-pyridytoxy)-phenoxy ] propionic acid methyl ester, and 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy] propionic acid butyl ester.
• the actions of these compounds are not always large enough.
• the object of the present invention is to obtain said compound industrially, to provide an improved herbicide meeting the needs of the market, and to provide a herbicidal process using said herbicide.
• the present invention relates to a novel derivative of phenoxypropionic acid ester (hereinafter referred to as the "compound of the present invention”) which can be represented by the following general structural formula [1]: wherein R, denotes a chlorine atom, bromine atom, trifluoromethyl group or nitro group; R2 denotes a hydrogen atom or chlorine atom; and A denotes a methine group or nitrogen atom, a manufacturing process of said derivative, a herbicide containing said derivative as the active constituent and a herbicidal process using said herbicide.
• R denotes a chlorine atom, bromine atom, trifluoromethyl group or nitro group
• R2 denotes a hydrogen atom or chlorine atom
• A denotes a methine group or nitrogen atom
• the compound of the present invention can be manufactured by various processes, typical ones of which are as follows:
• R denotes a chlorine atom, bromine atom, trifluoromethyl group or nitro group
• R2 denotes a hydrogen atom or chlorine atom
• A denotes a methine group or nitrogen atom
• Hal denotes a halogen atom
• M denotes a metal ion or ammonium ion.
• the compound of the present invention can be obtained by the above reactions either in the presence or in the absence of a reaction solvent.
• reaction solvents there can be used ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as ethyl ether, tetrahydrofuran and dioxane, halogenated hydrocarbons such as chlorobenzene, chloroform, carbon tetrachloride and dichloroethane, tertiary amines such as triethyl amine, pyridine and dimethylaniline, or polar solvents such as dimethylformamide, dimethylsulfoxide and hexamethyltriamide phosphate.
• ketones such as acetone and methyl ethyl ketone
• aromatic hydrocarbons such as benzene, toluene and xylene
• ethers such as ethyl ether
• the reaction can be carried out in the presence of a base.
• bases which can be used are tertiary amines such as triethyl amine, pyridine and dimethylaniline, alkali hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkaline carbonates such as sodium carbonate, potassium carbonate, sodium bi-. carbonate and potassium bicarbonate and metal hydrides such as sodium hydride.
• the reaction normally takes place at about 0°C to 150°C, preferably between about 20°C and about 100°C.
• the time required for the reaction ranges from several minutes to about 48 hours.
• the compound of the present invention in using the compound of the present invention as a herbicide, it can be used in any of the generally practiced forms such as an emulsion, a wettable powder, water soluble powder, oil soluble powder, dusting powder and as granules in combination with adjuvants. These formulations may be used either as they are or as dilutions (diluted to specified concentrations) with water, or on solid carriers.
• the adjuvants include, for example, diluents, extending agents, surface active agents, stabilizers, fixing agents, spraying agents for aerosols and synergists.
• solvents for diluents there can be used water, organic solvents, hydrocarbons halogenated hydrocarbons, alcohols, ethers, alcohol ethers, ketones, esters, amides and sulfoxides.
• inorganic dust and granules such as slaked lime, magnesia lime, gypsum, calcium carbonate, silica, pearlite, pumice, diatomaceous earth, alumina, zeolite, clay minerals (talc, vermicu- lite, kaolinite), vegetable dust and granules (starch, farina, grape sugar) and synthetic resin dust and granules (phenol resin, urea resin, vinyl chloride resin).
• the surface active agents there can be used anionic surface active agents (alkyl sulfate esters, aryl sulfonic acids, succinic acid salts, polyethylene glycol alkyl aryl ether sulfate esters), cationic surface active agents (alkyl amines and polyoxyethylene alkyl amines), nonionic surface active agents (polyoxyethylene glycol ethers, .polyoxyethylene glycol esters, polyhydric alcohol esters) and amphoteric surface active agents.
• anionic surface active agents alkyl sulfate esters, aryl sulfonic acids, succinic acid salts, polyethylene glycol alkyl aryl ether sulfate esters
• cationic surface active agents alkyl amines and polyoxyethylene alkyl amines
• nonionic surface active agents polyoxyethylene glycol ethers, .polyoxyethylene glycol esters, polyhydric alcohol esters
• amphoteric surface active agents there can be
• the quantity thereof may be varied depending on the form of the formulation, the method, object and time of application and the condition of the weeds.
• the compound of the present invention is used at the rate of 0.05 to 10 kg/ha, and preferably at 0.1 to 5 kg/ha.
• Soil was put in 1/5000 are Wagner's pots to create the upland condition, and certain quantities of the seeds of barnyard. grass, Japanese radish and soybean'were sowed. Then the soil in the pot was covered with a layer of soil about 1 cm in thickness containing the seeds of weeds of the Gramineae family such as the crab grass, barnyard grass, foxtail, etc. After 3 days from the sowing of the seeds, a liquid for spraying of a specified concentration was sprayed evenly on the soil. After 22 days from the treatment of the soil, the conditions of growth of the vegetables and the weeds were observed. The result are shown in Table 1. The values representing the degree of growth control (of the weeds) were classified into 5 grades (5 to 1) (5 denotes complete destruction, and 1 no effect).
• the compounds of the present invention have a satisfactory selectivity concerning vegetables such as beans, cotton, carrots, potatoes, beet, cabbage, mustard, peanuts, Japanese radish, tobacco, tomafoes,cucumbers, etc., and when these compounds (having the usual concentrations for the usual use) are applied for the pre-emergence treatment and post-emergence treatment of weeds, especially of the weeds of the Gramineae family, such'as barnyard grass, crab grass, goose grass, foxtail, wild oats, water foxtail, yellow foxtail, quack grass, Agropyron tsukushiens, Bermuda grass, Johnson grass, etc., they display an excellent selective herbicidal effect.
• the period of time required for the development of the activity of the compound is 4 to 5 days, which is much shorter than that of similar conventional compounds, and this is one of the outstanding features of each of the compounds of the present invention.

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• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Pyridine Compounds (AREA)

Applications Claiming Priority (2)

Publications (2)

Family

ID=13999194

Family Applications (1)

Country Status (2)

Cited By (2)

Family Cites Families (4)

• 1985
  • 1985-04-26 JP JP60090459A patent/JPS61249954A/ja active Pending
• 1986
  • 1986-04-24 EP EP86105688A patent/EP0201775A3/de not_active Withdrawn

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